| 15. Round | 14/01/2000 | Skoda Xanthi | - | Paniliakos Pyrgos | 1:0 | ||||
| 16. Round | 23/01/2000 | Paniliakos Pyrgos | - | Panachaiki GE | 0:0 |  |
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| 17. Round | 29/01/2000 | AO Proodeftiki | - | Paniliakos Pyrgos | 1:1 | ||||
| 18. Round | 05/02/2000 | Paniliakos Pyrgos | - | Panionios GSS | 3:0 |  |
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| 19. Round | 12/02/2000 | Paniliakos Pyrgos | - | Apollon Smyrnis | 2:1 | ||||
| 20. Round | 18/02/2000 | AO Kavala | - | Paniliakos Pyrgos | 2:1 | ||||
| 21. Round | 26/02/2000 | Paniliakos Pyrgos | - | AO Trikala | 1:3 | |
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| 23. Round | 10/03/2000 | Paniliakos Pyrgos | - | PAOK Saloniki | 0:4 | ||||
| 24. Round | 18/03/2000 | Panathinaikos | - | Paniliakos Pyrgos | 3:1 | ||||
| 25. Round | 25/03/2000 | Paniliakos Pyrgos | - | Ethnikos Asteras | 2:0 | ||||
| 26. Round | 01/04/2000 | Iraklis Saloniki | - | Paniliakos Pyrgos | 3:1 | |
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| 27. Round | 10/04/2000 | PS Kalamata | - | Paniliakos Pyrgos | 2:1 | ||||
| 28. Round | 15/04/2000 | Paniliakos Pyrgos | - | Olympiakos Piraeus | 0:3 | ||||
| 29. Round | 22/04/2000 | Ionikos Nikea | - | Paniliakos Pyrgos | 0:2 |
Costa Rica